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A tandem reaction is a reaction in which several bonds are formed in sequence without isolating intermediates. The tandem reaction below goes through three key reactions: a) a Suzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflate leaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Using your knowledge of metal-catalyzed coupling reactions, please answer the following questions. OMe Pd(PPh3)4 (or PdL4) LOR₁ NaOEt, THF (solvent), 50 °C R₁ = TBS 1) TBAF (TBS deprotection) 2) TfO₂, Et₂N PdL₂ cat. R₁ Tf Et,N, THF 60 °C OMe OH B. HO 1 R₁ =TBS (alcohol protecting group) The third and final step of this tandem reaction is a Heck-type coupling that follows the catalytic cycle below. Each step of the catalytic cycle has been named, please fill in the boxes with the structure of each key intermediate and populate the table with the number of L- and X-type ligands, oxidation state, d" notation, and total electron count for each metal complex (i-v). 5 (Product) HOTf L-Pd°-L i. Oxidative addition of 4 Reductive elimination H L-Pd-OTf +L 1 Catalyst regeneration 5 B-hydride elimination Ligand substitution ii. 1,2- Insertion iii. iv. Complex #X type ligands #L type ligands Pd Oxidation dn Notation Total electron State count i. ii. iii. iv.

A tandem reaction is a reaction in which several bonds are formed in sequence without isolating intermediates. The tandem reaction below goes through three key reactions: a) a Suzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflate leaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Using your knowledge of metal-catalyzed coupling reactions, please answer the following questions. OMe Pd(PPh3)4 (or PdL4) LOR₁ NaOEt, THF (solvent), 50 °C R₁ = TBS 1) TBAF (TBS deprotection) 2) TfO₂, Et₂N PdL₂ cat. R₁ Tf Et,N, THF 60 °C OMe OH B. HO 1 R₁ =TBS (alcohol protecting group) The third and final step of this tandem reaction is a Heck-type coupling that follows the catalytic cycle below. Each step of the catalytic cycle has been named, please fill in the boxes with the structure of each key intermediate and populate the table with the number of L- and X-type ligands, oxidation state, d" notation, and total electron count for each metal complex (i-v). 5 (Product) HOTf L-Pd°-L i. Oxidative addition of 4 Reductive elimination H L-Pd-OTf +L 1 Catalyst regeneration 5 B-hydride elimination Ligand substitution ii. 1,2- Insertion iii. iv. Complex #X type ligands #L type ligands Pd Oxidation dn Notation Total electron State count i. ii. iii. iv.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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help me with part b; fill in the circle, and the table

A tandem reaction is a reaction in which several bonds are formed in sequence without isolating intermediates. The tandem reaction below goes through three key reactions: a) a Suzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflate leaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Using your knowledge of metal-catalyzed coupling reactions, please answer the following questions. OMe Pd(PPh3)4 (or PdL.4) LOR₁ 3 NaOEt, THF (solvent), 50 °C R₁ = TBS 1) TBAF (TBS deprotection) 2) TfO2, Et₂N PdL₂ cat. R₁ = Tf Et,N, THF 60 °C Br он OMe 1 R₁ = TBS (alcohol protecting group) HO-B The third and final step of this tandem reaction is a Heck-type coupling that follows the catalytic cycle below. Each step of the catalytic cycle has been named, please fill in the boxes with the structure of each key intermediate and populate the table with the number of L- and X-type ligands, oxidation state, d" notation, and total electron count for each metal complex (i-v). 5 (Product) HOTf L-Pd°-L i. Oxidative addition of 4 Reductive elimination Н L-Pd-OTf L +L 1 5 Complex #X type ligands i. ii. iii. iv. Catalyst regeneration Ligand substitution -L B-hydride elimination 1,2- Insertion iv. ii. #L type Pd Oxidation dn Notation ligands State Total electron count
Transcribed Image Text:A tandem reaction is a reaction in which several bonds are formed in sequence without isolating intermediates. The tandem reaction below goes through three key reactions: a) a Suzuki-type coupling to generate 3, then b) deprotection of R₁ and installation of a triflate leaving group to generate 4, and finally c) a Heck-type coupling reaction to make 5. Using your knowledge of metal-catalyzed coupling reactions, please answer the following questions. OMe Pd(PPh3)4 (or PdL.4) LOR₁ 3 NaOEt, THF (solvent), 50 °C R₁ = TBS 1) TBAF (TBS deprotection) 2) TfO2, Et₂N PdL₂ cat. R₁ = Tf Et,N, THF 60 °C Br он OMe 1 R₁ = TBS (alcohol protecting group) HO-B The third and final step of this tandem reaction is a Heck-type coupling that follows the catalytic cycle below. Each step of the catalytic cycle has been named, please fill in the boxes with the structure of each key intermediate and populate the table with the number of L- and X-type ligands, oxidation state, d" notation, and total electron count for each metal complex (i-v). 5 (Product) HOTf L-Pd°-L i. Oxidative addition of 4 Reductive elimination Н L-Pd-OTf L +L 1 5 Complex #X type ligands i. ii. iii. iv. Catalyst regeneration Ligand substitution -L B-hydride elimination 1,2- Insertion iv. ii. #L type Pd Oxidation dn Notation ligands State Total electron count
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